1H-Pyrazole, 4-chloro- → HCID 90415524, 화합물

HRID 578850

반응식

HRID 578850 반응식
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9](Br)[C:10]([O:13][CH:14](F)F)=[N:11][CH:12]=2)[CH:5]=[N:4][CH:3]=[N:2]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[Cl:52][C:53]1[CH:54]=[N:55][NH:56][CH:57]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([N:55]3[CH:54]=[C:53]([Cl:52])[CH:57]=[N:56]3)[C:10]([O:13][CH3:14])=[N:11][CH:12]=2)[CH:5]=[N:4][CH:3]=[N:2]1

참가 물질

7

반응물 4

HCID 275241H-Pyrazole, 4-chloro-HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 90414984HCID 90414984, 화합물2회

생성물 1

HCID 90415524HCID 90415524, 화합물수율 46.5%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of 5-((1H-1,2,4-triazol-1-yl)methyl)-3-Bromo-2-methoxypyridine (Intermediate 13), (100 mg, 0.37 mmol), in toluene (5 mL) was added tris(dibenzylideneacetone)dipalladium(0) (34.1 mg, 0.04 mmol), sodium tert-butoxide (71.6 mg, 0.74 mmol), (2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (29.3 mgs, 0.07 mmol) and 4-chloro-1H-pyrazole (37.3 mg, 0.37 mmol). The mixture was heated at 100° C. for 30 min. The mixture was quenched with water (0.5 mL), diluted with ethyl acetate (10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 20-100% EtOAc/hexanes) afforded the title compound (50 mg, 46%). 1H NMR (400 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.07 (s, 2H), 8.01 (q, J=2.3 Hz, 2H), 7.99 (s, 1H), 5.37 (s, 2H), 3.94 (s, 3H), 2.52 (s, 1H). [M+H]=292.12.

후처리

  1. customThe mixture was quenched with water (0.5 mL)
  2. additiondiluted with ethyl acetate (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification (FCC, SiO2, 20-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-cea5b33739754b4e98db49361842ff56
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040692B2

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